HUP9901050A2 - Method for the synthesis of dioxolane nucleosides with betha-configuration - Google Patents
Method for the synthesis of dioxolane nucleosides with betha-configurationInfo
- Publication number
- HUP9901050A2 HUP9901050A2 HU9901050A HUP9901050A HUP9901050A2 HU P9901050 A2 HUP9901050 A2 HU P9901050A2 HU 9901050 A HU9901050 A HU 9901050A HU P9901050 A HUP9901050 A HU P9901050A HU P9901050 A2 HUP9901050 A2 HU P9901050A2
- Authority
- HU
- Hungary
- Prior art keywords
- synthesis
- betha
- configuration
- formula
- relates
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 239000002777 nucleoside Substances 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 abstract 1
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 abstract 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000003833 nucleoside derivatives Chemical class 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- IGFXRKMLLMBKSA-UHFFFAOYSA-N purine Chemical compound N1=C[N]C2=NC=NC2=C1 IGFXRKMLLMBKSA-UHFFFAOYSA-N 0.000 abstract 1
- 230000000707 stereoselective effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A jelen találmány biológiailag fontos, 1,3-dioxolán cukorgyűrűkettartalmazó nukleozidanalógok előállítására szolgáló eljárásokra éskompozíciókra vonatkozik. Nevezetesen, e találmány a b (cisz)-izomersztereoszelektív szintézisére vonatkozik, melynek során a bázist -amely egy purin- vagy pirimidinbázis, vagy ezek analógja vagyszármazéka - a (II) képlet szerinti köztitermékkel glikoziláljákkörülbelül -10 °C alatti hőmérsékleten, ahol a képletben az R1 egyhidroxil védőcsoport, és az L csoport halogén. ÓThe present invention relates to processes and compositions for the production of biologically important nucleoside analogs containing 1,3-dioxolane sugar rings. Namely, this invention relates to the stereoselective synthesis of the b (cis)-isomer, during which the base - which is a purine or pyrimidine base, or an analog or derivative thereof - is glycosylated with an intermediate according to the formula (II) at a temperature below approximately -10 °C, where R1 in the formula is a monohydroxy protecting group, and the L group is halogen. HE
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9525606.1A GB9525606D0 (en) | 1995-12-14 | 1995-12-14 | Method and compositions for the synthesis of dioxolane nucleosides with - configuration |
| PCT/CA1996/000845 WO1997021706A1 (en) | 1995-12-14 | 1996-12-13 | METHOD AND COMPOSITIONS FOR THE SYNTHESIS OF DIOXOLANE NUCLEOSIDES WITH β-CONFIGURATION |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HUP9901050A2 true HUP9901050A2 (en) | 2001-04-28 |
| HUP9901050A3 HUP9901050A3 (en) | 2001-05-28 |
| HU224076B1 HU224076B1 (en) | 2005-05-30 |
Family
ID=10785435
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9901050A HU224076B1 (en) | 1995-12-14 | 1996-12-13 | Method for synthesis of dioxolane nucleosides with betha-configuration |
Country Status (28)
| Country | Link |
|---|---|
| US (4) | US5922867A (en) |
| EP (1) | EP0970074B1 (en) |
| JP (1) | JP3229990B2 (en) |
| KR (1) | KR100406159B1 (en) |
| CN (1) | CN1080263C (en) |
| AP (1) | AP879A (en) |
| AT (1) | ATE214699T1 (en) |
| AU (1) | AU706328B2 (en) |
| BR (1) | BR9612351A (en) |
| CA (1) | CA2237730C (en) |
| DE (1) | DE69620042T2 (en) |
| DK (1) | DK0970074T3 (en) |
| EA (1) | EA000844B1 (en) |
| ES (1) | ES2172697T3 (en) |
| GB (1) | GB9525606D0 (en) |
| HK (1) | HK1017886A1 (en) |
| HU (1) | HU224076B1 (en) |
| IL (3) | IL124663A (en) |
| IN (1) | IN187349B (en) |
| MX (1) | MX9804701A (en) |
| NO (1) | NO309901B1 (en) |
| NZ (1) | NZ323855A (en) |
| OA (1) | OA11094A (en) |
| PL (1) | PL188447B1 (en) |
| PT (1) | PT970074E (en) |
| TW (1) | TW341574B (en) |
| WO (1) | WO1997021706A1 (en) |
| ZA (1) | ZA9610544B (en) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU6898498A (en) | 1997-04-07 | 1998-10-30 | Triangle Pharmaceuticals, Inc. | Use of mkc-442 in combination with other antiviral agents |
| KR100856416B1 (en) | 1998-08-12 | 2008-09-04 | 길리애드 사이언시즈, 인코포레이티드 | Method of Manufacture of 1,3-Oxathiolane Nucleosides |
| US6979561B1 (en) * | 1998-10-09 | 2005-12-27 | Gilead Sciences, Inc. | Non-homogeneous systems for the resolution of enantiomeric mixtures |
| ATE254126T1 (en) | 1998-12-23 | 2003-11-15 | Shire Biochem Inc | ANTIVIRAL NUCLEOSIDE ANALOGUES |
| JP2002538780A (en) * | 1999-02-11 | 2002-11-19 | シェア バイオケム インコーポレーテッド | Stereoselective synthesis of nucleoside analogs |
| US6583149B1 (en) | 1999-09-24 | 2003-06-24 | Biochem Pharma Inc. | Method for the treatment or prevention of viral infection using nucleoside analogues |
| US6566365B1 (en) * | 1999-11-04 | 2003-05-20 | Biochem Pharma Inc. | Method for the treatment of Flaviviridea viral infection using nucleoside analogues |
| WO2001058920A2 (en) * | 2000-02-10 | 2001-08-16 | Mitsui Chemicals, Inc. | Process for selectively producing 1-phosphorylated sugar derivative anomer and process for producing nucleoside |
| DE60127946D1 (en) | 2000-02-11 | 2007-05-31 | Shire Biochem Inc | A STEREOSELECTIVE METHOD FOR THE PRODUCTION OF NUCLEOSIDANALOGES |
| WO2002051852A1 (en) * | 2000-12-27 | 2002-07-04 | Mitsui Chemicals, Inc. | Process for producing nonnatural saccharide derivative |
| AU2002335489B2 (en) * | 2001-03-01 | 2008-06-05 | Abbott Laboratories | Polymorphic and other crystalline forms of cis-FTC |
| WO2003020222A2 (en) * | 2001-09-04 | 2003-03-13 | Merck & Co., Inc. | PYRROLO[2,3-d]PYRIMIDINES FOR INHIBITING RNA-DEPENDENT RNA VIRAL POLYMERASE |
| AU2002336864B2 (en) * | 2001-11-02 | 2006-08-17 | Shire Biochem Inc. | Pharmaceutical compositions for the treatment of leukemia comprising dioxolane nucleosides analogs |
| AU2002365234B2 (en) * | 2001-12-14 | 2009-01-29 | Pharmasset Inc | N4-acylcytosine nucleosides for treatment of viral infections |
| CA2473736C (en) * | 2002-01-25 | 2011-10-11 | Shire Biochem Inc. | Process for producing dioxolane nucleoside analogues |
| US6855821B2 (en) | 2002-08-06 | 2005-02-15 | Pharmasset, Ltd. | Processes for preparing 1,3-dioxolane nucleosides |
| EP1620479B1 (en) | 2002-10-15 | 2013-07-24 | ExxonMobil Chemical Patents Inc. | Polyolefin adhesive compositions and articles made therefrom |
| DE10335061B4 (en) * | 2003-07-31 | 2005-11-17 | Wacker-Chemie Gmbh | Process for the preparation of OH-protected [4- (2,6-damino-9H-purin-9-yl) -1,3-dioxolan-2-yl] methanol derivatives |
| CN105039489A (en) * | 2004-02-03 | 2015-11-11 | 埃莫里大学 | Methods to manufacture 1,3-dioxolane nucleosides |
| US7749531B2 (en) * | 2005-06-08 | 2010-07-06 | Indicator Systems International | Apparatus and method for detecting bacterial growth beneath a wound dressing |
| BRPI0813036A2 (en) * | 2007-07-30 | 2017-10-24 | Rfs Pharma Llc | stereoselective process for preparing purine dioxolane nucleoside derivatives. |
| CN101862676B (en) * | 2009-04-17 | 2012-01-25 | 中国石油化工股份有限公司 | Large-aperture SBA-15 mesoporous material-copper trifluoromethanesulfonate composite catalyst, preparation method and application |
| CN103288806A (en) * | 2013-07-02 | 2013-09-11 | 山东大学 | Synthesis method of troxacitabine |
| WO2018022263A1 (en) | 2016-07-29 | 2018-02-01 | Exxonmobil Chemical Patents Inc. | Polymerization processes using high molecular weight polyhydric quenching agents |
| JP7337539B2 (en) * | 2018-06-21 | 2023-09-04 | メディヴィル・アクチエボラーグ | Base-Modified Cytidine Nucleotides for Leukemia Therapy |
| WO2019245444A1 (en) | 2018-06-21 | 2019-12-26 | Medivir Ab | Base-modified cytidine nucleotides for leukemia therapy |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5276151A (en) * | 1990-02-01 | 1994-01-04 | Emory University | Method of synthesis of 1,3-dioxolane nucleosides |
| CZ123493A3 (en) * | 1992-06-22 | 1994-02-16 | Lilly Co Eli | Stereoselective anionic glycosylation process |
-
1995
- 1995-12-14 GB GBGB9525606.1A patent/GB9525606D0/en active Pending
-
1996
- 1996-12-13 CN CN96199879A patent/CN1080263C/en not_active Expired - Lifetime
- 1996-12-13 IL IL12466396A patent/IL124663A/en not_active IP Right Cessation
- 1996-12-13 JP JP52157397A patent/JP3229990B2/en not_active Expired - Lifetime
- 1996-12-13 AT AT96941539T patent/ATE214699T1/en not_active IP Right Cessation
- 1996-12-13 ES ES96941539T patent/ES2172697T3/en not_active Expired - Lifetime
- 1996-12-13 IN IN2810DE1996 patent/IN187349B/en unknown
- 1996-12-13 ZA ZA9610544A patent/ZA9610544B/en unknown
- 1996-12-13 PT PT96941539T patent/PT970074E/en unknown
- 1996-12-13 DK DK96941539T patent/DK0970074T3/en active
- 1996-12-13 EP EP96941539A patent/EP0970074B1/en not_active Expired - Lifetime
- 1996-12-13 DE DE69620042T patent/DE69620042T2/en not_active Expired - Lifetime
- 1996-12-13 AU AU10893/97A patent/AU706328B2/en not_active Expired
- 1996-12-13 CA CA002237730A patent/CA2237730C/en not_active Expired - Lifetime
- 1996-12-13 US US08/849,722 patent/US5922867A/en not_active Expired - Lifetime
- 1996-12-13 BR BR9612351A patent/BR9612351A/en not_active Application Discontinuation
- 1996-12-13 TW TW085115392A patent/TW341574B/en active
- 1996-12-13 NZ NZ323855A patent/NZ323855A/en unknown
- 1996-12-13 KR KR10-1998-0704473A patent/KR100406159B1/en not_active IP Right Cessation
- 1996-12-13 WO PCT/CA1996/000845 patent/WO1997021706A1/en active IP Right Grant
- 1996-12-13 PL PL96327443A patent/PL188447B1/en not_active IP Right Cessation
- 1996-12-13 EA EA199800555A patent/EA000844B1/en not_active IP Right Cessation
- 1996-12-13 IL IL14415596A patent/IL144155A/en not_active IP Right Cessation
- 1996-12-13 AP APAP/P/1998/001252A patent/AP879A/en active
- 1996-12-13 HU HU9901050A patent/HU224076B1/en active IP Right Grant
-
1998
- 1998-06-09 OA OA9800077A patent/OA11094A/en unknown
- 1998-06-11 MX MX9804701A patent/MX9804701A/en unknown
- 1998-06-12 NO NO982716A patent/NO309901B1/en unknown
-
1999
- 1999-02-17 US US09/251,431 patent/US6069250A/en not_active Expired - Lifetime
- 1999-05-17 HK HK99102184A patent/HK1017886A1/en not_active IP Right Cessation
-
2001
- 2001-07-05 IL IL14415501A patent/IL144155A0/en unknown
- 2001-11-16 US US09/987,845 patent/US20020058670A1/en not_active Abandoned
-
2002
- 2002-10-02 US US10/262,107 patent/US20030060476A1/en not_active Abandoned
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HFG4 | Patent granted, date of granting |
Effective date: 20050401 |